Over the past five seasons of Mad Men, costume designer Janie Bryant has so impressively outfitted Jon Hamm, January Jones, Christina Hendricks, and the rest of the cast in elegant styles evoking 60s Manhattan that she has inspired viewers to revisit fashions of the era. Since the drama’s inception on AMC, Michael Kors has cited Mad Men as a runway inspiration, Prada has taken a sartorial cue from the series, and the Tennessee-raised designer has collaborated on three collections with Banana Republic, making Sterling Cooper’s vintage office-wear accessible to contemporary consumers.

In anticipation of the show’s sixth season—premiering this Sunday!— VF.com phoned Bryant earlier this week to discuss the many character transformations that the Emmy winner has assisted with her indelible costumes.

Julie Miller:Matthew Weiner is notoriously tight-lipped about upcoming seasons ofMad Men. At what point does he tell you what will be happening during the season so that you can start preparing?

Janie Bryant: What happens is I usually get a five- or six-week period for prep time, and that’s when I start doing the costume designs. During that time, I have my creative discussions with Matt, and we talk about what’s going to happen for the upcoming season. At that point, I’ll know the time line, sort of. [Laughs.] It’s an ongoing process, but at the beginning, that’s where I start doing my research for whatever year it is. I’ll start by watching old movies of the period. I do a lot of research. I have a lot of costume- history books. I look at a lot of catalogues, like Montgomery Ward, Sears, and J.C. Penney, that are really about everyday living during that period. That is really important, because Mad Men is about portraying the lives of all of these different characters. It is not about a cat walk or trends of the 1960s. . . . It’s about developing characters through costume design that are real and natural to those specific people.

Some characters do experiment with trends, as we saw last season with Megan and Harry, for example. As the trends of the era approach more synthetic and Lurex, how do you toe the line of acknowledging the time period’s styles without veering into cheesy territory?

For me, it’s always by being inspired by the script and being really inspired by the characters. It’s so much about the mood of Mad Men as well. I always think of it as being very sophisticated and extremely intelligent. The tone can be dark and a little humorous. It’s never cheesy. I always keep that in mind for the costume design.

By Ron Jaffe/AMC.

What’s the most difficult aspect of designing for the show?

For me, it’s always about going from season to season and gently moving forward. And making sure that the seasons are tied together, but to show that time has passed as well. That always seems to be the biggest challenge. Going back to real life, it’s understanding that in our real life we know that the styles and the trends may change. Not all of us keep up with them. And not all of the trends may be best for our figure. There are certain characters that have changed. Megan is a character that could definitely change her style, between being an actress and leaving the office. There were all of these different roles for her to play. She was Don’s new wife and had a whole new income from that. She was able to afford very stylish clothing (left). So that was fun, to think about how her character could really change and grow.

Harry is another character who has really changed throughout all five seasons. I was just looking at some of Harry’s Season One and Season Two costumes. To look at him in Season Five and to see how his character has changed and grown from this newbie, insecure guy at the agency with the nerdy glasses and bow ties to . . . if there’s one character that is kind of cheesy and douchey [now], it’s Harry. In Season Five, we see him as Mr. Hollywood, getting into that modern style for men’s wear.

Did you have any inkling, while designing Jessica Paré’s “Zou Bisou Bisou” look, how big of a moment that would be for the show?

That was an incredible costume-design moment for Mad Men, for sure. I thought it was amazing that Megan was the first character to really wear a mini-dress onMad Men. I loved that. It was all part of the song and the dance and the movement. I loved the story it told about Megan, and also her relationship with Don. That it is this new, modern relationship. That says it all with the dress.

By Ron Jaffe/AMC.

Sally has really matured in terms of her character, her fashion sense, and her taste for white go-go boots. Can you talk about designing her transformation last season?

It’s been interesting, because I feel like Sally has two lives, as we saw in Season Five. She has her life in the Francis house and her life at Don and Megan’s. I really wanted to tell that story with her [costumes], to separate those two worlds. At Don and Megan’s house, it’s a little more fun and free. She can go shopping with Megan. At the Francis house, it’s definitely more traditional, preppy, and East Coast. It’s almost a repressed environment.

Not only that, but in seasons past, there has been a part of Sally’s character’s costume design that has been about mimicking Betty and trying to dress like Betty, but also having that rebellion against her. In Sally’s costumes, I always try to do opposing colors for her, like a lot of oranges and greens and reds and colors that Betty would never wear. I like having those two characters opposing each other, even though their silhouettes are sometimes similar. There was a scene, I think in Season Three, where Betty leaves the house, her house with Don, and is going to marry Henry. There is a shirtwaist dress—a plaid, winter shirtwaist dress that I designed for Betty. She goes up the stairs and she lays on Sally’s bed. Previously in that episode, Sally wears a plaid that is almost exactly like the dress I made Betty. But it has this amazing meaning, because it’s almost like Betty goes back to her childhood state to sort of reflect on leaving the house, and then she is lying down in almost the fetal position on Sally’s bed. It’s such a beautiful moment, design wise. I love the meaning of that scene but especially how Betty and Sally match each other as well.

Joan became more proactive at the agency last season and underwent a lot of personal changes, but maintained her taste in curve-hugging office-wear. Were there any transformations you mirrored in her wardrobe?

She has some progressions, but her figure really is suited for that fifties design and silhouette. Christina [Hendricks] and I always joke that Joan buys her clothing two sizes too small. It’s always about accentuating her hourglass. I’ve always seen her as this character who asserts herself in a very feminine way in the office. And she understands how to use those assets. She really holds onto that late-fifties moment. I always thought Joan’s style icons would be Marilyn Monroe and Sophia Loren. Those women who always exude sexiness.

By Ron Jaffe/AMC.

If Marilyn Monroe and Sophia Loren are Joan’s style icons, who are Peggy’s?

Well, I don’t think that Peggy has style icons. [Laughs.] I don’t think that that’s a bad thing! I just don’t think she is a character that cares about fashion. I think that she thinks she looks cute. I always see her as a character who understands what matching is, and thinks, “O.K. This goes together well. I’m wearing that.” It always comes from the motivation and intention of being put together enough. But there also has to be that modesty and earnest sensibility about that character. I think she is one of the most textured characters ofMad Men.

How difficult was it working around January Jones’s pregnancy and Betty’s curvier shape?

I can only tell you that I loved working with January. She totally has, in Season Five, a different figure. It was interesting to work with her character gaining weight and seeing how that would change what her character would wear. Still, Betty is a character who tries to be put together and look pretty. Also, she is the politician’s wife, as opposed to being the advertising executive’s wife. With that, there is a different façade of perfection, and it is almost more conservative. For Season Five, it was all about her pleat suits and beautiful blouses, and put-together looks and being inspired by Jackie Kennedy. I always felt that Betty would be reading every article she could about Jackie Kennedy at this time. [Laughs.]

What are the chances that Roger ditches his suit this season and goes through a groovy fringed vest phase?

Well, I can’t respond to that, but I think that that is part of Roger’s charm. I love that about Mad Men. That it is about maintaining the truth of these characters. How often do you see men’s change style, anyway? He does have little bits of flair—brocade ties, three points on his handkerchief, a pinky ring. But he is still a businessman and comes from that classic New York sensibility.

By Michael Yarish/AMC.

As I recall, Pete did have a major madras moment last season.

And Don! I do love a good sports-coat extravaganza for sure, especially when they are all plaid. That’s just the thing about men’s wear of that period. All the plaids and checks and herringbone and houndstooth. It was looked upon as normal. Men weren’t afraid to sport their loudest plaid jacket. I love that Megan really had the influence on Don wearing his plaid sports coat. That is one of my all-time favorite moments. People were so surprised to see Jon Hamm in a plaid sports coat. I just thought he looked so handsome.

What are the biggest changes you’ve made to Don’s wardrobe throughout the last five seasons?

Don Draper is a character that—in the flashbacks—when we see that Don came from being a car salesman to a fur salesman to working at the advertising agency—I always felt like he really, when he got into the advertising business, his suits were really about creating that façade of masculinity, elegance, and ambiguity. It’s much more about his suits being an armor for him. Because it’s always about hiding so many secrets. In all five seasons pretty much, it has been about secrecy and minimalism and creating that look of everything being perfect. I always thought it was interesting when he and Betty were married, because I think he and Betty really shared that façade of perfection.